4-(Tri­methyl­silyl)­benzoic acid

The title compound, C₁₀H₁₄O₂Si, crystallizes as a centrosymmetric O—H...O hydrogen-bonded dimer with two almost identical mol­ecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.063
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

(4)

Crystal data

C10H14O2Si	Z = 4
Mr = 194.30	F(000) = 416
Triclinic, P1	Dx = 1.185 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2858 (10) Å	Cell parameters from 7303 reflections
b = 12.2693 (17) Å	θ = 3.7–25.7°
c = 14.258 (2) Å	µ = 0.18 mm^−1
α = 96.528 (12)°	T = 100 K
β = 91.642 (13)°	Plate, colourless
γ = 93.932 (12)°	0.36 × 0.24 × 0.09 mm
V = 1089.2 (3) Å^3

Data collection

Stoe IPDS II two-circle diffractometer	4142 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω scans	θmax = 25.7°, θmin = 3.8°
Absorption correction: multi-scan (MULABS; Spek, 1990; Blessing, 1995)	h = −7→7
Tmin = 0.947, Tmax = 0.992	k = −14→14
12520 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.063	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0184P)^2] where P = (Fo^2 + 2Fc^2)/3
4142 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Si1	0.86442 (10)	−0.05512 (6)	0.19904 (5)	0.02352 (16)
C11	0.6192 (4)	−0.13944 (19)	0.22311 (17)	0.0338 (5)
H11A	0.5294	−0.1554	0.1652	0.051*
H11B	0.5401	−0.0988	0.2722	0.051*
H11C	0.6589	−0.2086	0.2446	0.051*
C12	1.0426 (4)	−0.02212 (19)	0.30671 (16)	0.0324 (5)
H12A	1.1700	0.0221	0.2916	0.049*
H12B	1.0849	−0.0905	0.3288	0.049*
H12C	0.9665	0.0194	0.3564	0.049*
C13	1.0134 (4)	−0.1303 (2)	0.10356 (16)	0.0344 (6)
H13A	0.9201	−0.1479	0.0468	0.052*
H13B	1.0596	−0.1984	0.1247	0.052*
H13C	1.1385	−0.0839	0.0890	0.052*
C1	0.7827 (3)	0.07754 (19)	0.15807 (15)	0.0232 (5)
C2	0.5826 (3)	0.08087 (18)	0.11211 (15)	0.0270 (5)
H2	0.4877	0.0166	0.1043	0.032*
C3	0.5210 (3)	0.17536 (18)	0.07809 (15)	0.0265 (5)
H3	0.3842	0.1755	0.0480	0.032*
C4	0.6570 (4)	0.2698 (2)	0.08754 (16)	0.0232 (5)
C5	0.8566 (3)	0.26956 (18)	0.13404 (15)	0.0259 (5)
H5	0.9503	0.3343	0.1420	0.031*
C6	0.9166 (3)	0.17437 (17)	0.16833 (15)	0.0244 (5)
H6	1.0522	0.1750	0.1996	0.029*
C7	0.5904 (4)	0.3714 (2)	0.05029 (16)	0.0234 (5)
O71	0.4088 (3)	0.36326 (13)	0.00510 (11)	0.0341 (4)
H71	0.3790	0.4256	−0.0079	0.041*
O72	0.7107 (3)	0.45841 (13)	0.06366 (10)	0.0313 (4)
Si1A	0.17042 (10)	0.56238 (5)	0.30504 (4)	0.02178 (15)
C11A	0.3147 (3)	0.66968 (18)	0.39183 (15)	0.0278 (5)
H11D	0.2640	0.6622	0.4553	0.042*
H11E	0.2875	0.7428	0.3749	0.042*
H11F	0.4682	0.6603	0.3908	0.042*
C12A	0.2657 (4)	0.57592 (19)	0.18459 (15)	0.0303 (5)
H12D	0.4195	0.5674	0.1836	0.045*
H12E	0.2369	0.6486	0.1672	0.045*
H12F	0.1909	0.5189	0.1394	0.045*
C13A	−0.1219 (3)	0.57797 (19)	0.30718 (17)	0.0321 (5)
H13D	−0.1717	0.5708	0.3709	0.048*
H13E	−0.1965	0.5207	0.2621	0.048*
H13F	−0.1515	0.6505	0.2897	0.048*
C1A	0.2284 (3)	0.42294 (19)	0.34061 (15)	0.0231 (5)
C2A	0.1064 (4)	0.37327 (18)	0.40571 (16)	0.0280 (5)
H2A	−0.0184	0.4062	0.4273	0.034*
C3A	0.1603 (3)	0.27734 (18)	0.44024 (15)	0.0273 (5)
H3A	0.0737	0.2455	0.4849	0.033*
C4A	0.3430 (3)	0.22788 (19)	0.40881 (15)	0.0206 (5)
C5A	0.4649 (3)	0.27367 (17)	0.34157 (15)	0.0236 (5)
H5A	0.5875	0.2395	0.3188	0.028*
C6A	0.4068 (3)	0.36969 (17)	0.30767 (14)	0.0240 (5)
H6A	0.4900	0.4000	0.2611	0.029*
C7A	0.4131 (4)	0.12849 (19)	0.44893 (16)	0.0220 (5)
O71A	0.2975 (2)	0.09673 (13)	0.51671 (11)	0.0305 (4)
H71A	0.3431	0.0392	0.5341	0.037*
O72A	0.5707 (2)	0.08171 (13)	0.41895 (11)	0.0296 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0204 (3)	0.0212 (4)	0.0294 (4)	0.0035 (3)	−0.0020 (3)	0.0046 (3)
C11	0.0265 (12)	0.0285 (13)	0.0489 (15)	0.0033 (10)	−0.0007 (11)	0.0149 (11)
C12	0.0308 (12)	0.0310 (13)	0.0360 (13)	0.0048 (10)	−0.0051 (10)	0.0066 (10)
C13	0.0260 (12)	0.0356 (14)	0.0416 (14)	0.0091 (10)	−0.0035 (10)	0.0010 (11)
C1	0.0216 (11)	0.0263 (15)	0.0224 (13)	0.0064 (10)	0.0023 (10)	0.0030 (11)
C2	0.0225 (11)	0.0235 (12)	0.0346 (13)	−0.0013 (9)	−0.0040 (9)	0.0054 (10)
C3	0.0227 (11)	0.0283 (13)	0.0296 (12)	0.0062 (10)	−0.0023 (9)	0.0066 (10)
C4	0.0258 (12)	0.0221 (13)	0.0225 (12)	0.0046 (10)	0.0016 (9)	0.0039 (10)
C5	0.0269 (12)	0.0211 (12)	0.0302 (13)	0.0005 (9)	0.0005 (9)	0.0055 (9)
C6	0.0194 (11)	0.0260 (12)	0.0282 (12)	0.0010 (9)	−0.0011 (9)	0.0057 (9)
C7	0.0279 (12)	0.0246 (14)	0.0182 (12)	0.0059 (10)	0.0025 (9)	0.0013 (10)
O71	0.0359 (10)	0.0325 (10)	0.0367 (9)	0.0107 (8)	−0.0077 (7)	0.0130 (8)
O72	0.0404 (10)	0.0239 (9)	0.0301 (9)	0.0026 (7)	−0.0021 (7)	0.0054 (7)
Si1A	0.0203 (3)	0.0200 (4)	0.0259 (4)	0.0032 (3)	0.0004 (3)	0.0049 (3)
C11A	0.0235 (11)	0.0234 (12)	0.0364 (13)	0.0019 (9)	0.0023 (9)	0.0024 (10)
C12A	0.0330 (12)	0.0263 (12)	0.0326 (13)	0.0025 (10)	0.0015 (10)	0.0077 (10)
C13A	0.0246 (12)	0.0285 (13)	0.0446 (14)	0.0069 (10)	−0.0015 (10)	0.0078 (11)
C1A	0.0265 (12)	0.0193 (14)	0.0234 (13)	0.0038 (10)	−0.0016 (10)	0.0007 (10)
C2A	0.0281 (12)	0.0253 (12)	0.0336 (13)	0.0113 (10)	0.0099 (10)	0.0088 (10)
C3A	0.0287 (12)	0.0287 (13)	0.0266 (12)	0.0060 (10)	0.0066 (10)	0.0079 (10)
C4A	0.0228 (11)	0.0185 (13)	0.0206 (12)	0.0016 (9)	−0.0010 (9)	0.0025 (9)
C5A	0.0217 (11)	0.0229 (12)	0.0270 (12)	0.0050 (9)	0.0016 (9)	0.0036 (9)
C6A	0.0257 (11)	0.0232 (11)	0.0241 (11)	0.0025 (9)	0.0043 (9)	0.0056 (9)
C7A	0.0239 (11)	0.0215 (14)	0.0205 (12)	0.0008 (10)	−0.0021 (9)	0.0033 (10)
O71A	0.0365 (9)	0.0273 (9)	0.0312 (9)	0.0093 (7)	0.0057 (7)	0.0130 (7)
O72A	0.0320 (9)	0.0264 (9)	0.0326 (9)	0.0094 (7)	0.0037 (7)	0.0084 (7)

Geometric parameters (Å, º)

Si1—C11	1.859 (2)	Si1A—C12A	1.856 (2)
Si1—C12	1.863 (2)	Si1A—C13A	1.861 (2)
Si1—C13	1.867 (2)	Si1A—C11A	1.868 (2)
Si1—C1	1.889 (2)	Si1A—C1A	1.894 (2)
C11—H11A	0.9800	C11A—H11D	0.9800
C11—H11B	0.9800	C11A—H11E	0.9800
C11—H11C	0.9800	C11A—H11F	0.9800
C12—H12A	0.9800	C12A—H12D	0.9800
C12—H12B	0.9800	C12A—H12E	0.9800
C12—H12C	0.9800	C12A—H12F	0.9800
C13—H13A	0.9800	C13A—H13D	0.9800
C13—H13B	0.9800	C13A—H13E	0.9800
C13—H13C	0.9800	C13A—H13F	0.9800
C1—C6	1.399 (3)	C1A—C2A	1.388 (3)
C1—C2	1.407 (3)	C1A—C6A	1.402 (3)
C2—C3	1.381 (3)	C2A—C3A	1.385 (3)
C2—H2	0.9500	C2A—H2A	0.9500
C3—C4	1.383 (3)	C3A—C4A	1.397 (3)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.403 (3)	C4A—C5A	1.388 (3)
C4—C7	1.490 (3)	C4A—C7A	1.492 (3)
C5—C6	1.387 (3)	C5A—C6A	1.390 (3)
C5—H5	0.9500	C5A—H5A	0.9500
C6—H6	0.9500	C6A—H6A	0.9500
C7—O72	1.258 (3)	C7A—O72A	1.240 (3)
C7—O71	1.287 (3)	C7A—O71A	1.304 (3)
O71—H71	0.8400	O71A—H71A	0.8400
C11—Si1—C12	111.58 (12)	C12A—Si1A—C13A	109.65 (11)
C11—Si1—C13	109.89 (11)	C12A—Si1A—C11A	109.74 (11)
C12—Si1—C13	109.20 (10)	C13A—Si1A—C11A	110.01 (10)
C11—Si1—C1	108.43 (10)	C12A—Si1A—C1A	110.04 (10)
C12—Si1—C1	108.89 (11)	C13A—Si1A—C1A	109.55 (11)
C13—Si1—C1	108.80 (11)	C11A—Si1A—C1A	107.81 (10)
Si1—C11—H11A	109.5	Si1A—C11A—H11D	109.5
Si1—C11—H11B	109.5	Si1A—C11A—H11E	109.5
H11A—C11—H11B	109.5	H11D—C11A—H11E	109.5
Si1—C11—H11C	109.5	Si1A—C11A—H11F	109.5
H11A—C11—H11C	109.5	H11D—C11A—H11F	109.5
H11B—C11—H11C	109.5	H11E—C11A—H11F	109.5
Si1—C12—H12A	109.5	Si1A—C12A—H12D	109.5
Si1—C12—H12B	109.5	Si1A—C12A—H12E	109.5
H12A—C12—H12B	109.5	H12D—C12A—H12E	109.5
Si1—C12—H12C	109.5	Si1A—C12A—H12F	109.5
H12A—C12—H12C	109.5	H12D—C12A—H12F	109.5
H12B—C12—H12C	109.5	H12E—C12A—H12F	109.5
Si1—C13—H13A	109.5	Si1A—C13A—H13D	109.5
Si1—C13—H13B	109.5	Si1A—C13A—H13E	109.5
H13A—C13—H13B	109.5	H13D—C13A—H13E	109.5
Si1—C13—H13C	109.5	Si1A—C13A—H13F	109.5
H13A—C13—H13C	109.5	H13D—C13A—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13A—H13F	109.5
C6—C1—C2	117.1 (2)	C2A—C1A—C6A	117.2 (2)
C6—C1—Si1	122.83 (16)	C2A—C1A—Si1A	121.57 (16)
C2—C1—Si1	120.04 (17)	C6A—C1A—Si1A	121.07 (18)
C3—C2—C1	121.6 (2)	C3A—C2A—C1A	122.3 (2)
C3—C2—H2	119.2	C3A—C2A—H2A	118.9
C1—C2—H2	119.2	C1A—C2A—H2A	118.9
C2—C3—C4	120.5 (2)	C2A—C3A—C4A	119.5 (2)
C2—C3—H3	119.8	C2A—C3A—H3A	120.3
C4—C3—H3	119.8	C4A—C3A—H3A	120.3
C3—C4—C5	119.4 (2)	C5A—C4A—C3A	119.7 (2)
C3—C4—C7	120.3 (2)	C5A—C4A—C7A	119.5 (2)
C5—C4—C7	120.3 (2)	C3A—C4A—C7A	120.8 (2)
C6—C5—C4	119.7 (2)	C4A—C5A—C6A	119.74 (19)
C6—C5—H5	120.2	C4A—C5A—H5A	120.1
C4—C5—H5	120.2	C6A—C5A—H5A	120.1
C5—C6—C1	121.8 (2)	C5A—C6A—C1A	121.6 (2)
C5—C6—H6	119.1	C5A—C6A—H6A	119.2
C1—C6—H6	119.1	C1A—C6A—H6A	119.2
O72—C7—O71	123.9 (2)	O72A—C7A—O71A	123.9 (2)
O72—C7—C4	119.7 (2)	O72A—C7A—C4A	121.2 (2)
O71—C7—C4	116.3 (2)	O71A—C7A—C4A	114.86 (19)
C7—O71—H71	109.5	C7A—O71A—H71A	109.5
C11—Si1—C1—C6	154.77 (18)	C12A—Si1A—C1A—C2A	−153.69 (19)
C12—Si1—C1—C6	33.2 (2)	C13A—Si1A—C1A—C2A	−33.1 (2)
C13—Si1—C1—C6	−85.7 (2)	C11A—Si1A—C1A—C2A	86.6 (2)
C11—Si1—C1—C2	−27.5 (2)	C12A—Si1A—C1A—C6A	31.4 (2)
C12—Si1—C1—C2	−149.08 (17)	C13A—Si1A—C1A—C6A	151.98 (18)
C13—Si1—C1—C2	92.00 (19)	C11A—Si1A—C1A—C6A	−88.31 (19)
C6—C1—C2—C3	0.3 (3)	C6A—C1A—C2A—C3A	2.4 (3)
Si1—C1—C2—C3	−177.55 (17)	Si1A—C1A—C2A—C3A	−172.77 (18)
C1—C2—C3—C4	0.7 (3)	C1A—C2A—C3A—C4A	−0.2 (4)
C2—C3—C4—C5	−1.5 (3)	C2A—C3A—C4A—C5A	−1.8 (3)
C2—C3—C4—C7	179.7 (2)	C2A—C3A—C4A—C7A	176.2 (2)
C3—C4—C5—C6	1.2 (3)	C3A—C4A—C5A—C6A	1.4 (3)
C7—C4—C5—C6	−180.0 (2)	C7A—C4A—C5A—C6A	−176.5 (2)
C4—C5—C6—C1	−0.1 (3)	C4A—C5A—C6A—C1A	0.8 (3)
C2—C1—C6—C5	−0.6 (3)	C2A—C1A—C6A—C5A	−2.7 (3)
Si1—C1—C6—C5	177.18 (16)	Si1A—C1A—C6A—C5A	172.49 (17)
C3—C4—C7—O72	176.3 (2)	C5A—C4A—C7A—O72A	−4.7 (3)
C5—C4—C7—O72	−2.6 (3)	C3A—C4A—C7A—O72A	177.3 (2)
C3—C4—C7—O71	−4.0 (3)	C5A—C4A—C7A—O71A	174.9 (2)
C5—C4—C7—O71	177.16 (19)	C3A—C4A—C7A—O71A	−3.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O71—H71···O72^i	0.84	1.82	2.643 (2)	166
O71A—H71A···O72A^ii	0.84	1.80	2.643 (2)	175

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z+1.